Last New Year’s Eve, in a time before widespread COVID vaccinations or therapeutics, I spent my evening playing a Star Wars drinking game with my roommate Erin and subsequently passing out before midnight. This year, fully vaccinated (and boosted!) we wanted to do something different.
Erin has been wanting to take myself and our other roommate Teresa (featured in this trip to Emerald Isle) to her hometown of Pittsburgh, Pennsylvania for years – and this New Year’s proved to be an ideal time. So, on December 30th we packed up our bags, met up with Erin’s fiancée Kevin in Virginia, and made the 8.5 hour journey from Chapel Hill, N.C. up to the City of Bridges.
After a suspiciously smooth and traffic-free entrance into the city, we immediately checked into our hotel: EVEN Hotel Pittsburgh Downtown. Between the four of us, we each paid about $150 to share a room for three nights. Considering it was still peak holiday season and the hotel was smack downtown, this was pretty good deal!
After settling in and changing into more fashion-forward and less car ride grunge-esque clothing, we walked the few short blocks over to Market Square (one of the main hubs of downtown filled with shops, bars and restaurants). At the time, this area was still positively festive with a giant tree and ice skating rink taking center stage. Plus, all the surrounding office buildings were glass which looked amazing with the lights!
As the four of us were getting pretty ravenous after a long car ride, we quickly set about looking for food; however, be warned. While there were many restaurants, even on a Thursday night, most had at least an hour-long wait. Thankfully, we decided to stop in to this more hole-in-the-wall restaurant and snag seats at the bar – effectively jumping the long queue. It was called The YARD and was self-identified as an American gastropub.
To my great delight, this establishment was known for it’s wide variety of grilled cheese sandwiches and tomato soup – my ultimate comfort foods. I went for the “Buffy The Mac Attack Slayer,” which was made up of cheddar cheese, buffalo chicken and creamy mac ‘n cheese. My travel partners ordered equally decadent meals and it’s safe to say we all rolled out of the restaurant in need of a walk.
Stretching our legs turned into a night stroll along the Point State Park – which is where Pittsburgh’s two rivers (the Monongahela and Allegheny) converge to lead into the Ohio River. As a big water lover, it was beautiful to walk these rivers at night. There was plenty of seating and outdoor space, making me think this is the perfect place to visit with a book or outdoor picnic during the warmer months.
We also stopped by a cool Christmas pop-up bar called the Jingle Bar – which was entirely decked out in wrapping paper. I was a little too full for a slightly overpriced beverage, but it was still cool to see!
After getting our fill of views, we hurried back to our hotel to get ready for what would be a VERY full New Year’s Eve.
When I travel, on the first full day, one could say I’m a WEE bit impatient to get the day started (hey, I know myself okay?). Not wanting to waste a second of the lone rain-rain free day in Pittsburgh, I trekked out on my own in search of coffee and cool architecture. The old courthouse by our hotel was a shining example of the old city mixed in with the new. I just love how old architecture looks crammed along skyscrapers and modern buildings.
I ended up at Gasoline Street Coffee Co., where I purchased some house-made chai which was very good. There, I found a nook, pulled out a book (you always need to travel with one!), and waited for the rest of my party.
When we were all adequately caffeinated, we hopped on the train right next to the coffee house to cross the river and make our way to the Monongahela Incline. This trolley-type car would take us up, up, up to get a better view of the city. Fun fact is that this incline is actually the oldest, continuously-operating “funicular railway” in the U.S. I didn’t know that was a thing, but it was indeed very cool! Like the slow-moving processional when you make your way to the peak of a rollercoaster.
From there, there were plenty of overlooks to see the City of Bridges in its full splendor.
I also got to step inside the Carnegie Library of Pittsburgh which was celebrating its 125th anniversary! The town at the peak of the incline was wonderful in itself with houses stacked along its hillside.
After a slow descent (round-trip fare was $3.50), we took our car over to the Strip District. Pittsburgh itself is very walkable with pretty decent public transit; however, if you do need to drive, we made it almost everywhere within 10 minutes (although there was a very suspicious lack of traffic due to the holiday).
Now, the Strip District has a pretty massive selection of coffee houses, restaurants, wine bars, and shops. But after stopping to admire the inside of the St. Stanislaus Kostka R. C. Church…
…We were there on a mission: to obtain sandwiches from the original Primanti Bros – a hometown staple. With walls covered with illustrations of famous Pittsburgh athletes, musicians, etc., most everything they serve is covered with coleslaw and French fries. Apparently fries on sandwiches is one of the city’s many identifiers – who knew?
I got a sausage and cheese sandwich with said toppings. It was huge, and once again I was rolled out of the restaurant.
From there, we meandered through fish markets, candy stores, and outdoor vendors (where I bought a Pittsburgh hockey tee – go Pens!)…
…Before driving over to Randyland. Per Google descriptions, this funky building is “Folk artist Randy Gilson’s landmark building, filled with vividly colored, upbeat murals & objects.” It’s a little out of the way, and isn’t a long excursion, but if you have a car or easy access, it’s definitely worth a poke through!
After A LOT of walking, we were able to head back to our hotel for a much-needed siesta before our dinner reservations at 8:30. We had made reservations at a little Asian restaurant called Yuzu Kitchen just a hop, skip and a jump from where we were staying. While we had to order quickly before the kitchen closed, their drinks we’re good, the food came out fast and was reasonably priced, and our waitress was very nice!
I enjoyed a generous portion of peanut noodles…
…And Teresa quickly ate a pepper from her General Tso dish and we subsequently watched her suffer for a solid 10 minutes. Below you can watch my concern turn to amusement. Sorry T!
After dinner, we plopped in the car to drive the 10 minutes to one of Kevin’s childhood friend’s homes to play games and casually ring in the New Year. A very pleasant evening!
After a late evening, we slept in on New Year’s Day and awoke to a very gloomy day. Unfortunately, a lot is closed on January 1st, so after perusing the streets in desperate need of coffee, we decided to head over to University of Pittsburgh’s campus (Pitt) to get some Dunkin’.
Now the area around Pitt is actually really cool! And they have a Harry Potter-esque library (that was also sadly closed) called the Cathedral of Learning which is definitely worth checking out.
From there, Kevin very nicely drove me over to Frick Park to pay homage to the late and great Mac Miller (a Pittsburgh native). Frick Park is home to the Blue Slide Park, which is the name of Mac’s first album. On Google Maps, they even have the slide dedicated to Mac. It was dubbed “The Blue Slide of Mac Miller” following his death in 2018.
In an attempt to escape the rain, we drove into the suburbs to visit Erin’s old workplace and popular Pittsburgh eatery “Burgatory.” Without Erin there working her magic, the service was pretty slow, but the gorgonzola fries and burgers were pretty banger. I built my own mushroom burger and AGAIN rolled out of the restaurant full to the brim. If you don’t eat your heart out in this city, you’re doing it wrong.
That evening, while Kevin was visiting his parents, the girls and I decided to take the T train to the North Shore to go to one of Erin’s favorite drinking establishments: Tequila Cowboy.
Side note: there are actually two Tequila Cowboys and now I’ve had the pleasure of patronizing both of them (the other of which is located in Nashville, TN where I spent my 21st birthday).
This place was pretty cool – split up into three rooms, there was a space dedicated for karaoke, a room with live country music, and another for 90s jams. Erin and I sang a song in the karaoke room, we watched a song or two in the country room, and danced by ourselves in the 90s room (the DJ could have been better) before we called it a night.
Call me old (or COVID conscious!) but I was not in the mood to chat with strangers (or strange men). For those looking to pick up hunnies in new cities, I would say the pickings are pretty slim in Pittsburgh unless you like weirdly country northerners with questionable fashion senses (not including Kevin of course – we love you!)
Even though it was sprinkling outside, we decided to walk along the Allegheny to get some last minute views in. The North Shore is almost directly across from Point State Park where we walked the first night. It was cool to see the city from a different angle. Erin said it’s one of her favorite hometown views!
After barely catching the final train home (through what was a very creepily deserted train station) we made our way back to the hotel. It was another great day not getting ax-murdered. The train was also free which was a nice plus!
The next morning was full of packing, gas station coffee and breakfast sandwiches, and the slow trek back through Virginia to North Carolina.
Overall, it was a lovely trip with tons of great views and eats with the best roommates (and Kevin) around. Also, since a lot was closed over the holiday, we left plenty more for next time! I know, personally, I’ll be going back to check out the Cathedral of Learning, La Gourmandine (a lovely French patisserie), and Amazing Books & Records (exactly what the name proclaims).
Until then!
xx, L
Great snapshot of pitt!